Regio- and diastereoselective S(N)2 ' or S(N)2 '' reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3

Authors
Maze, F Purpura, M Bernaud, F Mangeney, P Alexakis, A
Citation
F. Maze et al., Regio- and diastereoselective S(N)2 ' or S(N)2 '' reactions on chiral acetals of cyclic aldehydes promoted by PhCu, BF3, TETRAHEDR-A, 12(14), 2001, pp. 1957-1960
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
12
Issue
14
Year of publication
2001
Pages
1957 - 1960
Database
ISI
SICI code
0957-4166(20010814)12:14<1957:RADS'O>2.0.ZU;2-N
Abstract
The regio- and diastereoselectivity of the addition of PhCu, BF3 reagent on chiral acetals derived from several mono or dienic aldehydes was studied. It as found that monoethylenic acetals react regio- and diastercoselectivel y via Lin overall anti S(N)2' reaction. The regioselectivity observed with the dienic acetals seems to be strongly dependent on the nature of the acet al. In all cases the S(N)2'' reaction was the result of an anti process. (C ) 2001 Elsevier Science Ltd. All rights reserved.